4-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]piperidine-2,6-dione

Base Information

• Chemical Name: 4-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]piperidine-2,6-dione
• CAS No.: 6746-42-5
• Molecular Formula: C₁₅H₂₃NO₄
• Molecular Weight: 281.352
• Nikkaji Number: J75.655E,J31.348C
• Wikidata: Q27163592
• ChEMBL ID: CHEMBL225699
• Mol file: 6746-42-5.mol

Synonyms:Isocycloheximide;4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]piperidine-2,6-dione;D-Isocycloheximide;Caswell No. 504C;6746-42-5;EPA Pesticide Chemical Code 374700;17280-60-3;(+)-3-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide;4-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione;Glutarimide, 3-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (+)-;Cyclohemimide;Cyclohexamide;4-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)piperidine-2,6-dione;Actidione;Naramycin A;CHX;2,6-Piperidinedione, 4-((2R)-2-((1R,3R,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-;2,6-Piperidinedione, 4-[(2R)-2-[(1R,3R,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-;(Cycloheximide CHX);CHEMBL225699;MEGxm0_000238;SCHEMBL1714687;ACon0_000589;ACon1_002312;CHEBI:91792;YPHMISFOHDHNIV-UHFFFAOYSA-N;HMS3267I17;NSC 185;BCP28121;STL570292;AKOS015900576;NCGC00169964-01;NCGC00169964-02;NCGC00169964-03;NCGC00169964-04;LS-72054;BRD-A62184259-001-01-0;BRD-A62184259-001-02-8;Q27163592;3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl] glutarimide;3-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]glutarimide;2,6-Piperidinedione, 4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-, [1R-[1.alpha.(R*),3.alpha.,5.alpha.]]-;4-((2R)-2-((1S,3S,5S)-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-2,6-piperidinedione

Chemical Property of 4-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]piperidine-2,6-dione

Chemical Property:

• Vapor Pressure: 9.81E-12mmHg at 25°C
• Boiling Point: 491.8°Cat760mmHg
• Flash Point: 251.2°C
• PSA: 86.96000
• Density: 1.136g/cm³
• LogP: 1.31740
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 281.16270821
• Heavy Atom Count: 20
• Complexity: 404

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C(=O)C(C1)C(CC2CC(=O)NC(=O)C2)O)C

Technology Process of 4-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]piperidine-2,6-dione

There total 13 articles about 4-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]piperidine-2,6-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

C16H26N4O4 (3428-71-5,15676-38-7) → 4-[(S)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxo-cyclohexyl)-2-hydroxy-ethyl]-piperidine-2,6-dione (66-81-9,642-81-9,1154-57-0,3226-22-0,4630-75-5,5549-69-9,6258-25-9,6746-42-5,17280-60-3,17973-87-4,18006-33-2,29106-61-4,94130-62-8,94130-63-9,94799-82-3,95272-16-5,95272-17-6,95272-18-7)

Guidance literature:

With acetic acid; sodium nitrite; In water; at 0 ℃; for 0.25h; pH=5;

DOI:10.1016/S0040-4020(01)91400-0

Reference yield:

(2,6-dioxo-piperidin-4-yl)-acetaldehyde (2066-88-8) + (+)-(2S,4R)-trans-2,4-dimethyl-1-cyclohexanone (93921-42-7) → (2S,4S,6R,αS)-cycloheximide (94130-63-9) + (2S,4S,6S,αS)-cycloheximide (66-81-9,642-81-9,1154-57-0,3226-22-0,4630-75-5,5549-69-9,6258-25-9,6746-42-5,17280-60-3,17973-87-4,18006-33-2,29106-61-4,94130-62-8,94130-63-9,94799-82-3,95272-16-5,95272-17-6,95272-18-7) + Cycloheximide (642-81-9) + Cycloheximide (66-81-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1271/bbb1961.48.2315

Reference yield:

(2,6-dioxo-piperidin-4-yl)-acetaldehyde (2066-88-8) + ((4R,6S)-4,6-Dimethyl-cyclohex-1-enyloxy)-trimethyl-silane → (2S,4S,6R,αS)-cycloheximide (94130-63-9) + (2S,4S,6S,αS)-cycloheximide (66-81-9,642-81-9,1154-57-0,3226-22-0,4630-75-5,5549-69-9,6258-25-9,6746-42-5,17280-60-3,17973-87-4,18006-33-2,29106-61-4,94130-62-8,94130-63-9,94799-82-3,95272-16-5,95272-17-6,95272-18-7) + Cycloheximide (642-81-9) + Cycloheximide (66-81-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; Yield given. Yields of byproduct given; 1.) 20 deg C, 5 min, 2.) -45 deg C, 5 min;

DOI:10.1271/bbb1961.48.2315

upstream raw materials:

(2,6-dioxo-piperidin-4-yl)-acetaldehyde

(-)-(2R,4R)-cis-2,4-Dimethyl-1-cyclohexanone

(4R)-2,4-Dimethyl-1-cyclohexanone

Cycloheximide

Downstream raw materials:

C₁₆H₂₆N₄O₄

4-(2-methoxy-4-nitrophenoxy)butyl ester of 4-carbamoyl-3-(2-(3,5(S)-dimethyl-2-oxocyclohexylidene)ethyl)butanoic acid

N-(4-(2-methoxy-4-nitrophenoxy)-1-butyl)cycloheximide

N-(4-(2-methylamino-4-nitrophenoxy))butylcycloheximide